Bicarbonate Ion → HCID 9948616, compound

Participants

Reaction Steps

1-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(methylsulfanyl)ethanone (15.00 g, 50.94 mmol) is dissolved in CH2Cl2 (100 mL) in a flame-dried flask under argon then cooled in an ice/H2O bath. mCPBA (85%, 10.45 g, 51.47 mmol) is added carefully, generating some gas evolution of H2. The reaction is stirred for 1.75 h while maintaining the bath temperature until the last 20 minutes when the bath is allowed to warm. The reaction is then poured into saturated bicarbonate, separated and extracted with 2× CH2Cl2. The organics are concentrated on a rotavap then dried under vacuum (being careful of foaming). This gives a light tan foam which is purified by flash chromatography on silica with 1.6 L 27.5% acetone in hexanes then 100% acetone. A white solid is obtained which can be crystallized with EtOAc/hexanes with refrigeration to give white crystals, mp=143.6°-144.9° C.

Provenance & Evidence